


The Fourth Month

by bestGuesses



Category: Supernatural
Genre: Affairs, Anal Fingering, Anal Sex, Barebacking, Bottom Dean Winchester, Consensual Infidelity, Dean Winchester Has a Panty Kink, Dean Winchester in Lingerie, Desk Sex, Gay Sex, Infidelity, Lawyer Castiel (Supernatural), Loss of Virginity, Lube, M/M, Oral Sex, Panty Kink, Prostitute Dean Winchester, Prostitution, Sex, Smut, That's right, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester, Virgin Dean Winchester, dean's a prostitute AND a virgin, its fun
Language: English
Status: Completed
Published: 2019-10-01
Updated: 2019-10-01
Packaged: 2020-11-08 16:29:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,992
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20838575
Author URL: https://archiveofourown.org/users/bestGuesses/pseuds/bestGuesses
Summary: Dean likes not starving to death, and he likes it even more when Sam doesn't starve to death. Desperate times call for desperate measures, leaving Dean to take a Sharpie to the grimy wall of a bar's bathroom stall. He doesn't regret his decisions.





	The Fourth Month

Dean wasn’t sure of when he decided to start doing sex work. All he remembered was that Sammy needed food and petty theft wasn’t cutting it. Sure, maybe he had given the occasional blowjob for a quick few bucks, a handy in a bar bathroom for a 20, but things were different. Whatever he could pickpocket wasn’t getting them enough, people weren’t bidding as much when he was pool sharking, and Dean was really caught in a hole. So he decided to sell his own virginity to feed his brother. He swore up and down that it would be worth it. 

Sex couldn’t be that bad, right? 

The world was driven by it. Everywhere. Even on those damn soda advertisements on the beach with the half-naked women. It was down to basic biology, sex was the best way to sell. People had always told Dean he was pretty enough to try some modeling, so he figured that people might think he was attractive enough to actually pay well.

Dean was sure that his worst-case scenario would just be having a shitty client. Even then, he could do his job, take the cash, and never look back. He had scribbled his name and number on numerous bathroom stalls, and while it made him feel like a cheap whore (which, in all honesty, was exactly what he was aiming for) he knew he could at least get a few quick jobs. Dean had no intention of going into it seriously. Maybe a once or twice deal before he could figure something else out. 

He wasn’t going for the whole ‘standing on a street corner selling himself to any guy with a functioning dick’ look. 

Dean waited for a long while, silently hoping Sam wouldn’t find his phone and hear one of those calls. Most of the calls he got were pranks, people giggling as they tried to pretend to be a client. Dean was sure that his search was fruitless, hell, he was planning on backing out when he finally got the call.

It was seemingly inconspicuous, just a simple phone number. That didn’t stop the sinking feeling in his gut. Had a cop found him? Was CPS going to take Sam away from him? His head was racing as he slowly swiped his finger across the screen, holding the phone to his ear.

“Hello?” He asked, sitting down as he waited for a response.

“Dean Winchester?” A rough, unfamiliar voice on the other end of the phone asked.

“That’s me.”

“Novak Law Offices, tomorrow at five. We can discuss payment then.”

“Are you calling from the advertisements?” Dean asked, almost instinctively.

“No, I’m calling because your mother is at my home asking for extra butter.  _ Yes, _ I am calling over the ads,” the man hissed, “Are you in or not?”

“I… yes. I need a name, though.”

“Castiel Novak. Call me Cas,” the man stated before hanging up. Dean sat there, bewildered. He had actually gotten a real call. He took a few deep breaths, tapping his foot before nodding.

He had to get prepared.

***

Dean scrolled online for what seemed like ages. He was determined to get as much money as he could from the guy. He was a fucking  _ lawyer _ , and Dean knew that there was no way that man was running short on money, so he found himself browsing through lingerie. 

He had been staring at the screen so long his eyes glazed over before he  _ finally _ found a pair of panties. He grinned to himself as he checked sizes and prices, realizing that he could definitely spare a bit of money. They were forest green, satiny with black lace over the crotch around the edges. He knew he had hit the jackpot. Dean kept searching anyway, trying to see what else he could spot. He had never been happier to scroll down and find a garter belt with stockings. With a few more clicks and some extra cash for same-day shipping, Dean sat back in his chair.

He had actually managed to buy himself lingerie.

Dean knew that, as a child, the last thing he expected to do when he hit twenty was to sell himself out to whoever was horny enough to take him up on his offer, but he’d be damned if he didn’t do a great job doing it. Besides, maybe,  _ just  _ maybe, he’d have some fun himself.

Dean spent the next few hours watching porn. His dick gave an interested twitch, but he wasn’t trying to get off. Dean was trying to figure out how to actually have sex and seem experienced enough to not somehow fuck it up. He was fairly certain Sam would laugh his ass off if he found out that his brother was watching porn for  _ research _ , but Sam wasn’t there, so Dean was clear. 

He was in the midst of easily his thirtieth video when there was a knock on the shitty motel door. Dean stood slowly, walking over as an older man handed him the box and some papers to sign. He was avoiding eye contact, and Dean could feel his cheeks burning from embarrassment as he finalized the purchase. 

He had never been gladder to watch a delivery guy leave.

Dean sat down, his legs crossed as he opened the box with his pocket knife. Through all of the protective wrapping, he finally found the glint of green and grabbed his newest purchases. Dean laid everything out on the bed before stripping. He slipped the panties on, moving over to look at himself in the mirror. Dean smirked at the sight of himself. 

He knew he could pull the job off, and the panties were comfortable enough that he wouldn’t be faking confidence. Next came the belt and stockings, and he was glad to find that yeah, those stockings were  _ definitely _ perfect on his thighs. With a newfound sense of confidence in himself, Dean got dressed normally once more before flopping on his bed and passing out.

Dean quickly realized that he wasn’t as prepared as he thought.

The next morning, he awoke, still confident. He made himself breakfast, whistling his favorite Led Zeppelin song as he scrambled his eggs. By the time he was done fucking around, it was already noon. He had five hours to go, feeling the first wave of anxiety hit him. Dean brushed it off, going about his normal business.

Two hours later, Dean couldn’t brush it off. He couldn’t focus on watching TV no matter how hard he tried, and he couldn’t stop bouncing his leg nervously. What if Castiel was a creep? What if Castiel hurt him? What if he got robbed? Dean couldn’t seem to stop  _ thinking _ , and so he decided to start preparing. He stripped and headed to the bathroom to clean himself out, at least knowing that much about gay sex. He took a long shower, praying it would calm his nerves (it didn’t). He dressed in his lingerie, putting his clothes on over it, and  _ damn _ , he  _ still _ had half an hour left.

He was fucked.

Quite literally.

Dean opened his computer, deciding to try and answer some of his questions. All it took was a google search of Castiel Novak before he found some social media pages. The first thing Dean noticed was that Cas was  _ not _ slacking in the looks department. He looked clean, professional, and exactly like the kind of guy Dean would imagine when the internet was off and he had a hand down his pants. Dean searched for a while longer before freezing.

He had a  _ wife _ .

Dean really didn’t want to initiate infidelity, but he  _ really _ needed that damn money. He looked at a few pictures of Castiel’s wife, finding her name. 

April.

He was helping a lawyer cheat on a month.

Fabulous.

Dean ran a hand through his hair. He knew he could just not show up, but he had bought fucking  _ panties _ for the occasion. He glanced at the time.

4:30.

It was time to head out.

The drive was pretty long, Dean wasn’t exactly close to the office and he took multiple wrong turns. He couldn’t help it, he was nervous as hell. Soon enough, he was parking. The building was pretty large, two grand doors on either side with large windows adorning the walls. He swallowed the lump in his throat before heading in. A petite woman sat at the receptionist’s desk, and Dean quickly realized that it was  _ April _ .

“Hello, sir,” she greeted politely, a small smile on her face, “How may I help you?”

“I.. I have an appointment with Castiel Novak. Five o’clock.”

She nodded, clicking and typing before nodding.

“Dean Winchester?”

“That’s me.”

“Third floor, room 49,” April smiled. Dean offered a weak one in response before heading upstairs. His steps were reluctant, and he paused in front of the door. He could just make a run for it, head to his car and never look back.

But he bought panties.

The lingerie being the only force stopping Dean from stepping out, he knocked on the door.

“Enter,” a voice called from the other side. Dean turned the knob, stepped inside and closed the door securely behind himself.

Dean looked over at Castiel who seemed mostly impassive. He looked up at Dean.

“Call me sir.”

“I.. yes, sir,” Dean nodded.

Cas grinned, looking at Dean with hooded eyes. He examined his body as Dean shuffled on his heels from the scrutiny of his client's gaze. He kept his hands tucked securely behind his back.

"You don't normally do this, do you?"

"No, sir," Dean responded dutifully.

Cas stood slowly, stalking over and placing a gentle hand under his chin, tilting his head down enough so they were looking eye to eye. His gaze darkened as Dean nervously licked his lips.

"Good. What are your limits?”

Dean thought for a moment.

“Uh… watersports and scat. I.. I guess degradation too.”

Cas hummed in understanding.

“And... how much for  _ all _ of you? 300 upfront, 300 after?”

Dean’s eyes widened.

“I- that sounds good, sir.”

“Good,” Cas smiled, although Dean couldn't help but notice that unmistakable dark glint in his eyes. He reached into his pocket, grabbing his wallet before pulling out three crisp 100 dollar bills. Wrapping an arm around Dean’s waist and slipping the cash into his back pocket, he gave Dean’s ass a subtle squeeze before moving a hand up to curl in his hair, “On your knees.”

He nodded, shuffling down. After a moment of maneuvering, he sat on his heels. Cas ran his hand through Dean’s hair as he unzipped his own fly and unbuttoned his slacks. Dean steadied himself by grabbing Cas’ thighs, gently squeezing to feel the muscle. Cas was definitely lean, and even if Dean wasn’t getting paid, he’d definitely pick Cas up at the bar. Dean watched intently as Cas pulled his slacks down enough to show the outline of his hard cock, tugging at Dean’s hair a bit. Dean leaned in, mouthing at the side through the soft cotton as he lightly kneaded his thighs. Cas grinned, guiding his head with nimble fingers gently pulling at his hair. It wasn’t long before he was pulling his underwear down to his knees and Dean was taking the head of Cas’ cock into his mouth.

“Fuck,” Cas breathed, still gently petting Dean’s hair. Dean ran his tongue over the slit of Cas’ cock, causing him to audibly gasp. Dean willed himself to relax enough to not choke and die, because he was pretty sure that death was a turn off for most people, and Dean wanted to be alive to get paid that other $300. He couldn’t help but notice the slight stretching sting in the corners of his lips as he used his hand to stroke whatever he couldn’t reach. After a moment and numerous deep breaths through his nose, he finally began to bob his head, running his tongue along the underside as he gripped Cas’ thighs. Dean took a deep breath before relaxing himself as much as possible and taking all of Cas, staying there for a moment before pulling off with a small cough. Cas was about to ask if Dean was okay until his mouth was back on him, sucking his cock with vigor.

“So good. You’re perfect,” Cas pulled at his hair, a bit more harshly that time, but not enough to cause Dean any real pain. Dean hummed at the praise, clearly proud of himself. He pulled off of his cock with a light pop, standing up straight and beginning to unbutton Cas’ shirt. Dean really had no idea what to do from there, and Cas seemed to catch on as he undid the rest of his shirt, tugging the light fabric off of his shoulders until it was crumpled on the floor. Cas leaned in until they were practically breathing the same air, running a hand under the fabric of Dean’s shirt and up his back.

“Is kissing off limits?” Cas questioned.

“No, sir.”   
  


“Good,” he grinned before finally closing the distance between them. Dean moved a hand over Cas’ side, light traces of fingertips as Cas slowly pushed him toward the desk. Dean complied, stepping with Cas until the backs of his thighs were pressed against the wood and he could hardly move.

“Flip around,” Cas growled. Dean nodded, managing to turn himself around in the small space between Cas’ body and the desk. He was thankful that it was sturdy enough to support his weight as he leaned against it, quickly looking over the degrees on the wall. Cas leaned closer until his front was pressed against Dean, snaking a hand around him to unbutton his jeans. Cas pulled them down enough to see the shiny green fabric, and Dean held his breath.

“Holy shit,” Cas remarked, a smirk playing at the corners of his lips as Dean kicked his shoes off. At least, Dean assumed he was smirking, as he couldn’t help but notice the small change in tone whenever Cas was pleased with him. Dean quickly realized that he already knew  _ far _ too much about his client, and decided to just stick with focusing on Cas’ hands and the frames hanging neatly on the eggshell tone wall. With Cas’ assistance, Dean got his pants off. Cas cupped his ass with a sturdy hand, taking a deep breath. 

“God, you’re definitely worth more than 300,” he mumbled. Dean grinned a bit until Cas delivered a hard slap right above his thighs. His breath hitched as he gasped softly, leaning further against the desk and beginning to push some of the stacks of papers to the sides. Cas didn’t seem to mind, and neither did Dean. Cas spanked him a few more times as Dean keened, his thighs pressing harder against the desk and leaving red indents in the soft skin.

“Bend over,” Cas ordered. Dean managed to move the already disturbed stacks of paper, solely held together by loose paper clips. He noted a wooden pencil holder that he actually quite liked, but remembered that he really never used pencils anymore, and simply pushed that out of the way too. He bent over the desk, the firm wood supporting his already shaky legs. Cas traced the lace borders of his lingerie, soft fingertips roaming over scantily clad skin. 

“Safeword?”

“Impala.”

“Is that short enough for you?” Cas asked, clearly a bit concerned. Dean nodded.

“Yeah. ‘m fine,” he reassured. Cas nodded, although still Dean couldn’t see it, and began to hook his fingers under the lace and against Dean’s skin.

“The drawer right in front of you, other side of the desk. Lube,” Cas stated. Dean nodded, leaning over and fumbling before finding the small handle, rolling the drawer open before retrieving the bottle. It was unopened, and Dean heard the crunching of the plastic seal before the sound of the cap popping open. Cas pulled his panties down enough that Dean’s ass was on display, and he couldn’t help but feel a little self conscious. Still, Dean trusted Cas enough to allow himself that little bit of vulnerability. After all, when it came down to it, Dean  _ was _ in charge of the situation. One mumble of the word “impala” and Cas would get the message. Dean was just getting out of his little daydream when Cas moved a lube slicked finger around his rim, pressing and teasing without actually pushing in.

“Oh,  _ shit _ ,” Dean gasped a bit at the touch. Cas chuckled at his reaction.

“Relax, babe,” Cas instructed. Dean nodded, taking a few deep breaths. He managed to relax himself enough for Cas to push his finger in, making Dean wince a bit at the intrusion.

“Need more lube?” he asked. Dean nodded as Cas added a generous amount to his finger, working it in. Dean took a moment to relax again, mentally coaching himself to take deep breaths.

“Okay. All good.” 

Cas nodded as he slowly pushed his finger all the way in, making sure to keep his pace slow. He gradually sped up until Dean was pushing back against him, clutching the other end of the desk.

“More -” he choked out. Cas grinned, pulling his finger out. Dean whined at the loss as Cas lubed up a second finger. Right as Dean was about to speak, he was pushing two in at once. Dean didn’t take nearly as long to adjust, enthusiastically rocking back against Cas’ knuckles after only a few seconds. Dean tried to grind against the desk for some friction, but the wood wasn’t exactly forgiving, so Dean was left with trying to get more of Cas’ fingers. He hardly noticed when Cas added a third, other than a moment of pain. 

“Fuck-” Dean whined. Cas, still working his fingers to loosen Dean up, delivered a firm slap to his ass that left him whimpering.

“Don’t speak unless spoken to. Got it?”   
  


“Y-yes, sir,” Dean nodded. Cas gave a satisfied huff, pulling his fingers out. Dean heard the lube cap pop open once more along with a few seconds of silence. It wasn’t long before he felt something pressing against his rim, and Dean didn’t take long to realize what it was.

“ _ Please _ -” Dean gasped, trying to press his hips back. Cas made a small tsk-ing sound, spanking him once more.

“Shut up,” Cas ordered before pressing in. Dean inhaled sharply as Cas slowly bottomed out, a burning sensation stopping any pleasure. Cas was breathing heavily, stopping when his hips were pressed against Dean’s ass.

“Tell me when to move,” Cas breathed. Dean nodded, taking a few sharp breaths and considering asking for more lube, although he knew that the pain was probably because 3 fingers still wasn’t quite enough prep. Dean spent a few moments getting used to the feeling before nodding once more.

“Slow, sir,” Dean said. Cas hummed, pressing a hand on his lower back as he slowly pulled out. Dean wasn’t sure if he liked the feeling, and simply just kept breathing slowly. Cas maintained his slow pace until Dean started getting used to the feeling.

“Faster -” he nodded. Cas gently rubbed his back as he began to speed up a bit, Dean giving a few small gasps. It wasn’t long before he was trying to push back against Cas, panting heavily. Cas chuckled a bit, delivering another spank to his ass. Dean actually moaned at that, and Cas squeezed his ass as he fucked him faster.

“Fuck- holy hell-” Dean was pretty sure he was trying to say something, but it was incredibly hard to focus when he had a sex god fucking him over a desk. Cas chuckled, moving his hands to grip Dean’s hips as he very subtly changed position. Still, that small change was enough for Cas to hit his prostate, making Dean arch his back with a gasp.

“Right there- holy shit-” Dean nodded, bucking his hips every time Cas hit his prostate. As Cas sped up, Dean matched his pace with his small bit of mobility, pushing back against him. Cas had begun panting himself, curling a hand in Dean’s hair and forcing him somewhat upright. Dean nearly came just from the pull, clutching the desk. Cas’ pace was relentless, sharp hip bones slamming into Dean’s ass repeatedly, and Dean quickly decided that he absolutely  _ loved _ the feeling. Cas splayed his free hand over his back, somehow fucking him harder. Dean tried his best to spread his legs a bit further.

“You’re  _ tight _ ,” Cas remarked as Dean nodded, his breathing erratic. He shut his eyes, throwing his head back a bit as he focused on the feeling of Cas fucking him, moving a hand to his own cock. Cas slapped his ass once more, making Dean jump.

“Don’t touch yourself. You’ll cum on my cock alone or not at all.”

“I- yes-” Dean moved his hands away from himself. Normally, he’d be certain that he’d need something on his dick to get off, but with the way Cas was hitting his prostate on every thrust, Dean was tempted to test that belief. He could feel himself barreling to the edge, the only things keeping him grounded were his white-knuckled grip on the desk and Cas’ bruising hold on his hips.

“I’m close- Ca-  _ sir _ -” Dean swiftly corrected. Cas chuckled, his laugh breathy.

“Me too,” Cas squeezed his ass, and Dean was pretty sure he’d feel it for a week, “I want you to scream my name as you’re cumming, Dean.”

“Yes- yes sir,” Dean all but moaned as Cas pulled him upright so he was nearly standing. With a few more hard, well-timed thrusts, Dean was seeing stars.

“Cas!” he nearly screamed as he came, clutching the desk as Cas bit down on his shoulder, finishing inside of him. Dean was breathing heavily as he finally started seeing straight once more, practically limp in Cas’ arms. Dean took a moment to regain his bearings before standing properly, Cas pulling out of him. Dean stumbled a bit, his legs feeling practically like jelly. Cas rushed over to hold him up with a small chuckle.

“Thank you.”

“Of course. Get dressed,” Cas handed him his shirt and jeans. Dean nodded, pulling his panties back up and deciding to get cleaned up at home. He slipped his shirt back on, following it with his jeans as Cas got dressed too. 

The silence between them was comfortable, the only noise filling the room being the quiet sounds of cloth ruffling and Dean’s occasional wince when his ass came in contact with about anything. Being spanked and fucked definitely wasn’t the ideal pain reliever, but Dean didn’t mind. Hell, he even liked the ache and sting. After a few more moments of silence, Dean decided that he actually enjoyed Cas’ company, although he knew it was likely a one time deal. He knew Cas was just in it to get off, and he was in it to get paid. It was a fair deal, but Dean certainly hadn’t been expecting to get attached. He was really just thankful that he had the willpower to walk away without looking back. At least, he thought he did. Cas walked over, slipping another 300 in his hand before looking him in the eye.

“Let me take you to dinner.”

Dean paused, raising an eyebrow as he opened his mouth to object

“But- your wife-”

“April?” Cas chuckled, “Our marriage has been dead for years. We haven’t divorced because of our reputations. She’s with a man and a woman right now, and I doubt she gives a single shit about who I’m having sex with. So have dinner with me,” Cas stated before quickly adding, “Please.”

Dean smiled a bit at the admission, pocketing the cash before nodding.

“Yeah, of course dude,” he smiled.

“On me,” Cas grinned.

Dean made a mental note to buy another pair of panties.


End file.
